GB1461734A - Carbonxylic acids processes for their preparation and compostions - Google Patents

Carbonxylic acids processes for their preparation and compostions

Info

Publication number
GB1461734A
GB1461734A GB254375A GB254375A GB1461734A GB 1461734 A GB1461734 A GB 1461734A GB 254375 A GB254375 A GB 254375A GB 254375 A GB254375 A GB 254375A GB 1461734 A GB1461734 A GB 1461734A
Authority
GB
United Kingdom
Prior art keywords
general formula
coor
prepared
hydrogen atom
alkanoic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB254375A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1461734A publication Critical patent/GB1461734A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/88—Unsaturated compounds containing keto groups containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1461734 # - (3<SP>1</SP> - Benzoyl)phenyl - alkanoic and -alkenoic acid derivatives ROUSSELUCLAF 21 Jan 1975 [24 Jan 1974] 2543/75 Headings C2C and C2P Novel # - (3<SP>1 </SP>- benzoyl)phenyl - alkanoic and -alkenoic acid derivatives of the general formula wherein Z is a straight, saturated or monoethylenically unsaturated aliphatic hydrocarbon chain having 4-17 carbon atoms, each of X<SP>1</SP>, X<SP>2</SP>, X<SP>3</SP> and X<SP>4</SP> is a hydrogen or halogen atom or a C 1-5 alkyl, C 1-5 alkoxy, C 1-5 alkylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio group and R is a hydrogen atom or a salifying base or esterifying alcohol residue, are prepared (a) when Z is -(CH 2 ) m -CH=CH-(CH 2 ) p -, in which m is 0-15, p is 0-15 and m+p = 2- 15, and R is a hydrogen atom or alkyl group, by subjecting an aldehyde of the general formula wherein the rectangular block symbol represents the X<SP>1</SP>, X<SP>2</SP>, X 3 , X<SP>4</SP>-substituted 31-benzoylphenyl moiety, to a Wittig reaction with a triphenylphosphorus compound of the general formula Ph 3 P = CH(CH 2 ) p COOR<SP>1</SP>, wherein R<SP>1</SP> is a hydrogen atom or alkyl group; (b) when Z is -(CH 2 ) n - and n is 4-17, by catalytically hydrogenating the product of (a); (c) when Z is -CH 2 CH = CHCH 2 - and R is a hydrogen atom, by hydrolysing the corresponding nitrile; and (d) when Z is -CH 2 CH=CH(CH 2 ) 2 - and R is a straight or branched C 1-6 alkyl group (R 2 ), by condensing a chloride of the general formula with CH 3 COOR<SP>2</SP> in anhydrous tetrahydrofuran; followed optionally by salification, hydrolysis, esterification, saponification or transesterification of the product. Nitriles of the general formula are prepared by treating a chloride of the general formula given under (d) above with a nitrilating agent. Aldehydes of the second general formula above are prepared by catalytically reducing the corresponding carboxylic acid chloride. Triphenylphosphonium halides of the general formula Ph 3 P<SP>(+)</SP>CH 2 (CH 2 ) p COOR<SP>1</SP>Hal<SP>(-)</SP> (Hal is a halogen atom) are prepared by reacting triphenylphosphine with Hal-CH 2 (CH 2 ) p -COOR<SP>1</SP>. Pharmaceutical compositions having analgesic and antiinflammatory activity comprise, as active ingredient, at least one #-(3<SP>1</SP>-benzoyl)- phenyl-alkanoic or -alkenoic acid derivative of the first general formula above (the derivative being non-toxic in the case of a salt or ester), in association with a suitable pharmaceutical vehicle.
GB254375A 1974-01-24 1975-01-21 Carbonxylic acids processes for their preparation and compostions Expired GB1461734A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7402386A FR2278331A1 (en) 1974-01-24 1974-01-24 NEW CARBOXYLIC ACIDS AND THEIR DERIVATIVES, THEIR APPLICATION AS MEDICINAL PRODUCTS AND THEIR PREPARATION PROCESS

Publications (1)

Publication Number Publication Date
GB1461734A true GB1461734A (en) 1977-01-19

Family

ID=9133926

Family Applications (1)

Application Number Title Priority Date Filing Date
GB254375A Expired GB1461734A (en) 1974-01-24 1975-01-21 Carbonxylic acids processes for their preparation and compostions

Country Status (20)

Country Link
US (1) US4337353A (en)
JP (1) JPS50101345A (en)
AT (1) AT338767B (en)
BE (1) BE824658A (en)
CA (1) CA1060039A (en)
CH (1) CH605570A5 (en)
DD (1) DD115485A5 (en)
DE (1) DE2502967A1 (en)
DK (1) DK671674A (en)
ES (1) ES434066A1 (en)
FR (1) FR2278331A1 (en)
GB (1) GB1461734A (en)
HU (1) HU168548B (en)
IE (1) IE41831B1 (en)
IL (1) IL46402A (en)
LU (1) LU71700A1 (en)
NL (1) NL7500785A (en)
SE (1) SE7416057L (en)
SU (5) SU645551A3 (en)
ZA (1) ZA75292B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4992576A (en) * 1987-01-12 1991-02-12 Eli Lilly And Company Intermediates for leukotriene antagonists
US5235064A (en) * 1987-01-12 1993-08-10 Eli Lilly And Company Leukotriene antagonists
US5171882A (en) * 1987-01-12 1992-12-15 Eli Lilly And Company Leukotriene antagonists
FR2651494B1 (en) * 1989-09-05 1993-01-08 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ARYL-2 PROPIONIC ACIDS.
US4996230A (en) * 1990-02-16 1991-02-26 Eli Lilly And Company Leukotriene antagonists
GB9408994D0 (en) * 1994-05-06 1994-06-22 Vanguard Medica Ltd Compounds
FR2755965B1 (en) * 1996-11-19 1998-12-18 Cird Galderma BIAROMATIC COMPOUNDS, PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM AND USES
US6334889B1 (en) 1999-09-01 2002-01-01 Praxair Technology, Inc. Bed restraint for an adsorber

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1546478A (en) * 1967-01-27 1968-11-22 Rhone Poulenc Sa New derivatives of 3-benzoylphenylacetic acid and their preparation
GB1226344A (en) * 1967-07-31 1971-03-24
FR1584915A (en) * 1968-10-07 1970-01-02
FR8440M (en) * 1968-12-10 1971-07-15
US3657430A (en) * 1969-06-25 1972-04-18 Merck & Co Inc Composition and methods for treating inflammation
US3898275A (en) * 1970-11-20 1975-08-05 Sandoz Ag M-Substituted benzophenones
BE788316A (en) * 1971-09-03 1973-03-01 Roussel Uclaf NEW DERIVATIVES OF BUTYRIC ACID AND METHOD OF PREPARATION
FR2233039B1 (en) * 1973-06-14 1976-07-02 Roussel Uclaf
FR2292467A1 (en) * 1974-11-28 1976-06-25 Roussel Uclaf NEW DERIVATIVES OF BENZOPHENONE, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS A MEDICINAL PRODUCT

Also Published As

Publication number Publication date
ATA42075A (en) 1977-01-15
SU645552A3 (en) 1979-01-30
BE824658A (en) 1975-07-22
CA1060039A (en) 1979-08-07
DD115485A5 (en) 1975-10-05
LU71700A1 (en) 1975-12-09
SU637076A3 (en) 1978-12-05
HU168548B (en) 1976-05-28
FR2278331B1 (en) 1978-07-28
AT338767B (en) 1977-09-12
SU602111A3 (en) 1978-04-05
IE41831L (en) 1975-07-24
ZA75292B (en) 1976-02-25
DK671674A (en) 1975-09-29
IE41831B1 (en) 1980-04-09
IL46402A0 (en) 1975-04-25
JPS50101345A (en) 1975-08-11
DE2502967A1 (en) 1975-07-31
NL7500785A (en) 1975-07-28
ES434066A1 (en) 1977-03-01
US4337353A (en) 1982-06-29
SE7416057L (en) 1975-07-25
CH605570A5 (en) 1978-09-29
FR2278331A1 (en) 1976-02-13
AU7752875A (en) 1976-07-22
SU645551A3 (en) 1979-01-30
IL46402A (en) 1978-10-31
SU619098A3 (en) 1978-08-05

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee